Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

11. Radical Reactions

Anti Markovnikov Addition of Br

Organic Chemistry

11. Radical Reactions

Anti Markovnikov Addition of Br

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Problem 25a

Textbook Question

Predict the major products of the following alkene halogenation reactions. [D is the symbol for deuterium, an isotope of hydrogen.]
(a)

Verified step by step guidance

Identify the type of reaction: The reaction involves an alkene and HBr in the presence of H2O2, which indicates a radical addition reaction.

Understand the mechanism: In the presence of peroxides (H2O2), HBr adds to alkenes via a radical mechanism, leading to anti-Markovnikov addition.

Determine the regioselectivity: In anti-Markovnikov addition, the bromine atom will add to the less substituted carbon of the double bond.

Analyze the structure: The alkene shown is 2-methyl-2-butene. The double bond is between the second and third carbon atoms.

Predict the major product: The bromine will add to the terminal carbon (carbon 3), and the hydrogen will add to the more substituted carbon (carbon 2), resulting in the formation of 2-bromo-2-methylbutane.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Alkene Reactivity

Alkenes are unsaturated hydrocarbons characterized by at least one carbon-carbon double bond. This double bond is a site of high reactivity, allowing alkenes to undergo various addition reactions, such as halogenation. In these reactions, halogens (like Cl2 or Br2) add across the double bond, resulting in the formation of vicinal dihalides.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX (where X is a halogen) to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms already attached. This principle helps predict the major product of the reaction, as it favors the formation of the more stable carbocation intermediate during the reaction process.

Stereochemistry of Halogenation

Halogenation of alkenes can lead to stereochemical outcomes, including the formation of enantiomers or diastereomers. The addition of halogens typically occurs in a trans fashion, resulting in anti-addition products. Understanding the stereochemical implications is crucial for predicting the specific isomers formed in the reaction.

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Related Practice

Textbook Question

What alkyl halide will be obtained in greatest yield? Ignore stereoisomers.

Textbook Question

What alkyl halide will be obtained in greatest yield? Ignore stereoisomers.

Textbook Question

What five-carbon alkene forms the same product whether it reacts with HBr in the presence of a peroxide or with HBr in the absence of a peroxide?

Textbook Question

Write the propagation steps for the addition of HBr to 1-methylcyclohexene in the presence of a peroxide

Textbook Question

Predict the major products of the following alkene halogenation reactions. [D is the symbol for deuterium, an isotope of hydrogen.]

(b)

Textbook Question

Provide the expected product for the reaction of each of the following alkenes with (i) HBr and (ii) HBr, H₂O₂.

(e)

Textbook Question

Which reagent system (HBr or HBr, H₂O₂) would you use to carry out the following transformations?

(c)

Textbook Question

Predict the product of the following alkene addition reactions.

(b)

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Predict the major products of the following alkene halogenation reactions. [D is the symbol for deuterium, an isotope of hydrogen.](a)

Key Concepts

Alkene Reactivity

Markovnikov's Rule

Stereochemistry of Halogenation

Watch next

Predict the major products of the following alkene halogenation reactions. [D is the symbol for deuterium, an isotope of hydrogen.]
(a)